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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:36 UTC
HMDB IDHMDB0059624
Secondary Accession Numbers
  • HMDB59624
Metabolite Identification
Common Namealpha-L-Fucose
Descriptionalpha-L-Fucose, also known as 6-deoxy-alpha-L-galactose, is a hexose deoxy sugar. alpha-L-Fucose is a substrate for fucose mutarotase.
Structure
Data?1563865956
Synonyms
ValueSource
alpha-L-FucChEBI
alpha-L-FucpChEBI
a-L-FucGenerator
Α-L-fucGenerator
a-L-FucpGenerator
Α-L-fucpGenerator
a-L-FucoseGenerator
α-L-fucoseGenerator
6-Deoxy-L-galactopyranoseHMDB
6-Deoxy-L-galactoseHMDB
6-Deoxy-alpha-L-galactopyranoseHMDB
6-Deoxy-alpha-L-galactoseHMDB
6-Deoxy-α-L-galactopyranoseHMDB
6-Deoxy-α-L-galactoseHMDB
alpha-L-FucopyranoseHMDB
alpha-L-FucoseHMDB
α-L-FucopyranoseHMDB
α-L-FucoseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional Nameα-L-fucose
CAS Registry Number6696-41-9
SMILES
C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
InChI KeySHZGCJCMOBCMKK-SXUWKVJYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-2.4ALOGPS
logP-1.9ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-73abedcfedce730de924JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-5f2bd8fc908e0f2d17d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-9000000000-4ae8072a5651434f44b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-e7a20de995c932bdb5d1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-6900000000-03f10dd2373a0985cc0eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ef6b887ff1a4477de1fJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04473
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439554
PDB IDNot Available
ChEBI ID42548
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang TW, Gorbach SL, Bartlett JG: Inhibition of binding of Clostridium difficile toxin by steroids. J Infect Dis. 1980 Jul;142(1):113. [PubMed:6772711 ]
  2. Neethling FA, Koren E, Ye Y, Richards SV, Kujundzic M, Oriol R, Cooper DK: Protection of pig kidney (PK15) cells from the cytotoxic effect of anti-pig antibodies by alpha-galactosyl oligosaccharides. Transplantation. 1994 Mar 27;57(6):959-63. [PubMed:8154046 ]

Enzymes

General function:
Not Available
Specific function:
Involved in the interconversion between alpha- and beta-L-fucoses. L-Fucose (6-deoxy-L-galactose) exists as alpha-L-fucose (29.5%) and beta-L-fucose (70.5%), the beta-form is metabolized through the salvage pathway. GDP-L-fucose formed either by the de novo or salvage pathways is transported into the endoplasmic reticulum, where it serves as a substrate for N- and O-glycosylations by fucosyltransferases. Fucosylated structures expressed on cell surfaces or secreted in biological fluids are believed to play a critical role in cell-cell adhesion and recognition processes.
Gene Name:
FUOM
Uniprot ID:
A2VDF0
Molecular weight:
16764.555
Reactions
alpha-L-Fucose → beta-L-Fucosedetails